Potassium Hydroxide → HCID 53740207, compound

HRID 1603657Notes

Reaction equation

HRID 1603657 reaction equation
[CH2:1]([S:8][C@H:9]1[N:12]([CH2:13][C:14]([O:16]CC2C=CC(OC)=CC=2)=[O:15])[C:11](=[O:26])[C@@H:10]1[Br:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CO>[CH2:1]([S:8][C@H:9]1[N:12]([CH2:13][C:14]([OH:16])=[O:15])[C:11](=[O:26])[C@@H:10]1[Br:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54129709HCID 54129709, compound

Product 1

HCID 53740207HCID 53740207, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of p-methoxybenzyl [(3S, 4R)-4-benzylthio-3-bromo-2-oxoazetidin-1-yl]acetate (3.03 g, 0.0067 mol) in methanol (50 ml) at -5 to -10° C. a 1M solution of potassium hydroxide (7.4 ml) was added dropwise with stirring. After 2 h, the methanol was evaporated off and the residue diluted with water, extracted twice with ether, and the aq. layer acidified with ice cooling to pH 3 (2M HCl). The oil which precipitated soon crystallised and was filtered, washed and dried to give the title compound, yield 0.9 g (41%), m.p. 138-40° C.

Workup

  1. customthe methanol was evaporated off
  2. additionthe residue diluted with water
  3. extractionextracted twice with ether
  4. customThe oil which precipitated soon
  5. customcrystallised
  6. filtrationwas filtered
  7. washwashed
  8. customdried

Sources & evidence

ORD record
ord-f0c478bd975649ac80ae44c3362a86e7
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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